Condensed blending agent and lubricant



Patented Aug. 23, 1938 2,128,109

UNITED STATES PATENT OFFICE CONDENSED BLENDING AGENT AND LUBRICANT Peter J. Wiezevich, Elisabeth, N. J., assignor to Standard Oil Development Company, a corporation of Delaware No Drawing. Application September 28, 1934,

Serial No. 745,942

12 Claims. (Cl. 8l9) This invention relates to high molecular weight to remove the aluminum chloride, and the solvent oils or blending agents for hydrocarbons, and is distilled oii and the residue reduced to 600 F. more particularly to high molecular weight 0011- to remove unreacted Wax; the fixed chlorine may densation products capable of improving the be removed by steam distillation, heating with properties of lubricating and other oils. sodium, etc., then the residue can be employed In U. S. Patent 1,815,022 issued to G. H. B. as such as a lubricant or as a blending agent in Davis, a method was disclosed for preparing pour lubricants or fuels. In many cases, the crude inhibitors by the condensation of long chain hydrolyzed product is sufliciently satisfactory so aliphatic chlorinated hydrocarbons with aroas to dispense with the de-chlorinating step.

10 matic hydrocarbons. This invention covers the If a more potent product is desired, it may be 10 production of products having a similar effect, concentrated by precipitation of the more active but prepared by the condensation of chlorinated high molecular constituents by means of hot allong chain aliphatic compounds, preferably those cohols, ketones, light hydrocarbons which dissolve containing over 10 or carbon atoms, with subthe inactive ingredients.

15 stituted aromatic or cyclic hydrocarbons; that Various modifications of the method of reac- 15 is, with aromatic or cyclic hydrocarbons containacting these materials are possible. For instance, ing oxygen, sulfur; and similar non-hydrocarbon the chlorinated aliphatic compound and the oxyelements such as the ethers, thio-ethers, and nated romat yd b y be heated other similar derivatives. The term condensafirst for about 1-4 hours at ISO-140 F. before the tion" is employed to denote a chemical reaction addition of aluminum chloride. Furthermore, in- 20 of the Friedel and Crafts type, preferably constead of emp y the Friedel and -S reacducted at low temperatures. tion, a Wurtz synthesis of the chlorinated all- It is especially preferred to use oxygenated aro- D at p d with e nated o y-a matic compounds, and in particular, the aromotlc may be carried out in p n f s dium.

matic or cyclic ethers, such as diphenyl oxide, dia combination of Wurtz a Friedel a 26 phenylene-oxide, dicyclohexyl ether, dinaphthyl Crafts y be p y h form r n rally oxide, butyl phenyl ether, condensed or polymerbeing preferred for final nd ati ized diphenyl oxide, and the like. Similar com- In all of these reactions, the purpose is to conpounds such as those containing sulphur, selenidense the substituted aromatic compound with 30 um or tellurium may be used in addition to or the chlorinated long chain aliphatic compound to 30 substituted for the oxygen-containing comproduce a high molecular weight substantially pounds mentioned above. The above compounds non-volatile mp nd ontainin xy or may be described as others having at least one some other substituent besides carbon and hydrocyclic hydrocarbon radical and are described by s n. I i pr l to produce condensation the following formula: R X- R', whe R, is products having a molecular weight well above 35 hydrocarbon radical which may either be cyclic about 1000 or 2000 or higher. The substituent. or open chain. R is a cyclic hydrocarbon radical h as xy is preferably presen n e pr and X is a negative element of the 6th group of uct to the extent of 2 to 5 to 10 to 20% or more. the periodic table. One of the most valuable properties possessed 40 In the preferred method of producing these by the produ t obtained according to this in- 40 blending agents, paraflln wax or any other long vention is their ability to lower the pour points of chain aliphatic compound capable of condensing oils containing suspended solids of the wax type. with aromatics is halogenated to a chlorine or For this purpose the condensation product is other halogen content of approximately 8 to 15% added to the oil in concentrations of 0.01 to 0.5

or more. This product is then dissolved with an to 1 or 5% or more, depending upon the strength 45 equivalent amount of a substituted aromatic of the'pour inhibitor. This pour inhibiting propcompound of the class described above in an inerty is especially marked in the case of the high ert solvent such as hydrogenated or aluminum molecular weight viscous non-volatile residue, chloride treated heavy naphtha, and the mixture while the lower molecular weight extracts or volis treated ,with aluminum chloride or other simiatile components are most advantageously em- 50 hr condensing agent, and the temperature is ployed as lubricants. maintained below about 70 C. and preferably The product prepared according to this inveni'rom 20 to 35 C. After about 5 hours reaction tion also possesses exceptionally good lubricating time, the mixture is hydrolyzed with water, alcoand other similar properties making it very suit- 5 hol or other suitable hydrolyzing agent, in order able as a lubricant, cable oil, transformer 011, de-

waxing aid, and as a constituent in textile or soluble oils, and the like. It is obtained from the reaction mixture as a light colored, clean oil, differing in this respect from most condensation products of this type.

It also may be employed together with any or all of the following types of blending agents: Polymer thickeners capable of raising the viscosity and/or viscosity index of oils, bright stocks and other residuals, pour inhibitors such as Parafiow, oxidation inhibitors such as alpha naphthol, aromatic amines, sulfur and sulfur compounds. etc.; oiiiness agents, as, for example, oxidized wax, synthetic esters, etc.; 011 soluble and insoluble soaps, extreme pressure lubricating agents, oil soluble resins, sludge dispersing agents such as condensation products of petrolatum wax with naphthalene, etc.; metallo-organic compounds, dyes, cellulose derivatives, volatilized products, and the like.

The condensation products obtained according to this invention may be added to crude petroleum and its fractions, either waxy or dewaxed, lubricating oils either partially or highly refined, hydrogenated oils, aluminum chloride treated oils, solvent extracted oils, white oils, synthetic oils, greases, volatilized oils, glyceride oils, oils derived from coal, lignite, peat, and the like. They may also be used as or in top cylinder lubricants, and as blending agents in fuels and light distillates.

The following example will illustrate some of the many phases of this invention:

Example 400 gms. of chlorinated parafiln containing 11% chlorine was condensed with 60 gms. of diphenyl oxide in presence of 10 gms. of aluminum chloride while in solution in 300 gms. of heavy naphtha. The temperature was maintained at 32 C. for 5 hours, and upon hydrolysis of the reaction mixture with water, and distillation of the solvent, a residual oil was recovered having a molecular weight of approximately 500 and containing about 3% oxygen. This product had a viscosity of 211 seconds Saybolt at 210 F. and a viscosity index of 117, and lowered the pour of a waxy petroleum lubricating oil from 30 to 5 F. in 1% concentration.

Although I have shown and described certain specific embodiments of my invention, I am aware that many modifications thereof are pos- CERTIFICATE Patent No. 2,128 ,109.

sibie. My invention, therefore, is not to be restricted except insofar as is necessitated by the prior art and by the spirit of the appended claims.

I claim:

1. An improved lubricating oil of low pour point comprising a waxy hydrocarbon oil and a small quantity of a polymer condensation product of a waxy hydrocarbon and an ether containing at least one cyclic hydrocarbon radical.

2. A lubricating oil according to claim 1 in which the condensation product is obtained from an ether having at least one aromatic radical.

3. A lubricating 011 according to claim 1 in which the condensation product is obtained from a dicyclo ether.

4. A lubricating oil according to claim 1 in which the condensation product is obtained from a dicycio aromatic ether.

5. A lubricating oil according to claim 1 in which the condensation product is obtained from diphenyl ether.

6. A lubricating oil according to claim 1 in which the condensation product is obtained from diphenylene oxide.

'1. A lubricating oil of low pour point comprising a waxy hydrocarbon 'oil and a small quantity of a condensation product of an aliphatic organic compound having a chain of at least 10 carbon atoms and a thio ether containing at least one cyclic radical.

8. A lubricating oil according to claim '7 in which a dicyclic thio ether is used.

9. A lubricating oil according to claim "I in which a dicyclo aromatic ether is used.

10. A lubricating oil according to claim -'I', in which diphenylene thio ether is used.

11. A lubricating oil oi low pour point, comprising a viscous waxy hydrocarbon oil and a small quantity of a polymer-condensation product obtained by the union of a long chain aliphatic hydrocarbon with an ether-like substance of the following formula: RrX-R where R is a hydrocarbon radical, R is a cyclic hydrocarbon radical and X is an element selected from the sixth group of the periodic table of elements consisting of oxygen, sulfur, selenium and teiurium.

12. A lubricating oil as specified in claim 11 wherein the long chain aliphatic hydrocarbon has at least ten carbon atoms.

PETER J. WIEZEVI'CH.

or CORRECTION.

August 25, 1958.

It is hereby certified that the name of the inventor in the above numbered patent was erroneously described and specified as Peter J. Wiezevich, whereas said name should have been described and specified as Peter J wiezevich of Elizabeth, New Jersey, now by change of name Peter John Gaylor, as shown by the record of assignments in this office; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office Signed and sealed this 11th day of October, A. D. 1938.

( Seal) Henry Van Aredale Acting Commissioner of Patents.

waxing aid, and as a constituent in textile or soluble oils, and the like. It is obtained from the reaction mixture as a light colored, clean oil, differing in this respect from most condensation products of this type.

It also may be employed together with any or all of the following types of blending agents: Polymer thickeners capable of raising the viscosity and/or viscosity index of oils, bright stocks and other residuals, pour inhibitors such as Parafiow, oxidation inhibitors such as alpha naphthol, aromatic amines, sulfur and sulfur compounds. etc.; oiiiness agents, as, for example, oxidized wax, synthetic esters, etc.; 011 soluble and insoluble soaps, extreme pressure lubricating agents, oil soluble resins, sludge dispersing agents such as condensation products of petrolatum wax with naphthalene, etc.; metallo-organic compounds, dyes, cellulose derivatives, volatilized products, and the like.

The condensation products obtained according to this invention may be added to crude petroleum and its fractions, either waxy or dewaxed, lubricating oils either partially or highly refined, hydrogenated oils, aluminum chloride treated oils, solvent extracted oils, white oils, synthetic oils, greases, volatilized oils, glyceride oils, oils derived from coal, lignite, peat, and the like. They may also be used as or in top cylinder lubricants, and as blending agents in fuels and light distillates.

The following example will illustrate some of the many phases of this invention:

Example 400 gms. of chlorinated parafiln containing 11% chlorine was condensed with 60 gms. of diphenyl oxide in presence of 10 gms. of aluminum chloride while in solution in 300 gms. of heavy naphtha. The temperature was maintained at 32 C. for 5 hours, and upon hydrolysis of the reaction mixture with water, and distillation of the solvent, a residual oil was recovered having a molecular weight of approximately 500 and containing about 3% oxygen. This product had a viscosity of 211 seconds Saybolt at 210 F. and a viscosity index of 117, and lowered the pour of a waxy petroleum lubricating oil from 30 to 5 F. in 1% concentration.

Although I have shown and described certain specific embodiments of my invention, I am aware that many modifications thereof are pos- CERTIFICATE Patent No. 2,128 ,109.

sibie. My invention, therefore, is not to be restricted except insofar as is necessitated by the prior art and by the spirit of the appended claims.

I claim:

1. An improved lubricating oil of low pour point comprising a waxy hydrocarbon oil and a small quantity of a polymer condensation product of a waxy hydrocarbon and an ether containing at least one cyclic hydrocarbon radical.

2. A lubricating oil according to claim 1 in which the condensation product is obtained from an ether having at least one aromatic radical.

3. A lubricating 011 according to claim 1 in which the condensation product is obtained from a dicyclo ether.

4. A lubricating oil according to claim 1 in which the condensation product is obtained from a dicycio aromatic ether.

5. A lubricating oil according to claim 1 in which the condensation product is obtained from diphenyl ether.

6. A lubricating oil according to claim 1 in which the condensation product is obtained from diphenylene oxide.

'1. A lubricating oil of low pour point comprising a waxy hydrocarbon 'oil and a small quantity of a condensation product of an aliphatic organic compound having a chain of at least 10 carbon atoms and a thio ether containing at least one cyclic radical.

8. A lubricating oil according to claim '7 in which a dicyclic thio ether is used.

9. A lubricating oil according to claim "I in which a dicyclo aromatic ether is used.

10. A lubricating oil according to claim -'I', in which diphenylene thio ether is used.

11. A lubricating oil oi low pour point, comprising a viscous waxy hydrocarbon oil and a small quantity of a polymer-condensation product obtained by the union of a long chain aliphatic hydrocarbon with an ether-like substance of the following formula: RrX-R where R is a hydrocarbon radical, R is a cyclic hydrocarbon radical and X is an element selected from the sixth group of the periodic table of elements consisting of oxygen, sulfur, selenium and teiurium.

12. A lubricating oil as specified in claim 11 wherein the long chain aliphatic hydrocarbon has at least ten carbon atoms.

PETER J. WIEZEVI'CH.

or CORRECTION.

August 25, 1958.

It is hereby certified that the name of the inventor in the above numbered patent was erroneously described and specified as Peter J. Wiezevich, whereas said name should have been described and specified as Peter J wiezevich of Elizabeth, New Jersey, now by change of name Peter John Gaylor, as shown by the record of assignments in this office; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office Signed and sealed this 11th day of October, A. D. 1938.

( Seal) Henry Van Aredale Acting Commissioner of Patents. 

